Florida rentals in Islamorada, Florida

The Moorings Village is a charming lodging institution located at 123 Beach Road in Islamorada, Florida, United States. Nestled in a picturesque seaside setting, this luxurious retreat offers guests a tranquil and rejuvenating escape from the hustle and bustle of everyday life. With its beautifully appointed accommodations, lush tropical gardens, and pristine white sandy beaches, The Moorings Village provides the perfect backdrop for a relaxing vacation or romantic getaway. Whether you are seeking a peaceful retreat or an adventurous beach vacation, The Moorings Village offers a unique and unforgettable experience for all who visit.

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys. The resort features spacious and well-appointed rooms, a sparkling swimming pool, and stunning views of the surrounding landscape. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Topsiders Resort is the perfect destination for your next trip to paradise. With its convenient location and top-notch amenities, this resort is sure to provide a memorable and enjoyable experience for all guests.

Easy Livin Adventures is a premier travel agency located at 81576 Overseas Highway in Islamorada, Florida. Led by the world famous Captain Augie, a local legend with over two decades of experience in offshore fishing, Easy Livin Adventures offers custom boat tours that are sure to create lasting memories. Captain Augie, known for his sense of humor and larger than life personality, is more than just a tour guide - he is the missing element of fun your vacation needs. He will personally assist and advise you on the best use of your time in Islamorada, ensuring that you have an unforgettable experience.

Caribbean Catering, located at 80925 Overseas Highway in Islamorada, Florida, offers a wide range of affordable Florida Keys wedding planning and catering services. Specializing in Islamorada weddings and Keys sunset beach weddings, we strive to personalize every detail to make your special event truly unique. Our professional and friendly team works together to ensure that your guests are taken care of and that the food is excellent. From discussing decor and cake options to providing stress-free planning, we are dedicated to making your wedding day a dream come true. With a one-stop shop approach, we cover all the details from planning to clean-up, making us the perfect choice for your Islamorada wedding. Contact us today to see how we can make your event unforgettable.

Indian Key Historic State Park is a unique and historic institution located on an offshore island in Islamorada, Florida, United States. Accessible only by kayak launch, this park offers a glimpse into the past as it was once the first county seat for Dade County in 1836. The island was a hub for salvaging cargo from shipwrecks in the Florida Keys, making it a lucrative business at the time. Today, visitors can enjoy swimming, sunbathing, and hiking on the island. Kayak rentals are available from local charter companies for those looking to explore the area by water. Please note that as of Sept. 29, 2021, the boat ramp at Indian Key Fill is closed due to storm damage, and the observation tower is also closed. Park fees can be paid in cash at the iron ranger near the kayak launch or in advance using the "Pay Online Single-Use Day Pass" link. Visit Indian Key Historic State Park for a unique and educational experience in the beautiful Florida Keys.

Drop Anchor Resort & Marina is a charming lodging establishment located at 84959 Overseas Highway in the beautiful Islamorada, Florida. This waterfront resort offers a serene and relaxing escape for guests looking to unwind and enjoy the stunning views of the Florida Keys. With comfortable accommodations, a marina for boat enthusiasts, and a range of amenities including a pool and beach access, Drop Anchor Resort & Marina is the perfect destination for a memorable vacation in the heart of the Keys.

Casa Morada is a luxurious boutique lodging located on a quiet side road in Islamorada, Florida. Our property features 16 suites spread across two guest houses, the Garden House and the Seaview House. Guests can enjoy complimentary breakfast, use of kayaks, paddle boards, and bicycles, as well as yoga sessions on select days. Conveniently situated between Miami and Key West, Casa Morada is easily accessible by car or boat. We are a pet-friendly establishment and welcome children aged 16 and older. Each suite is uniquely designed and offers a range of amenities, from private terraces and soaking tubs to panoramic views of the water and private island.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean. The resort is designed as a peaceful tropical village, with oceanfront cottages and suites for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle that embodies the essence of Keys life. The resort boasts an oceanfront climate-controlled pool for relaxation, as well as seasonal yoga classes for rejuvenation. With personalized service and genuine hospitality, guests are welcomed as family at Pines and Palms Resort. Visitors can take advantage of complimentary kayaks, paddle boards, and bike rentals, as well as sunset sails and private fishing charters for added adventure.

Matecumbe Resort is a lodging institution located at 76261 Overseas Highway in Islamorada, Florida, United States. Situated on an oceanfront setting, our resort offers 32 recently remodeled units with fully equipped in-suite kitchens. Each unit includes a microwave, stove, refrigerator, pots & pans, toaster, and coffee maker. Additionally, all rooms feature a seating area with a sleeper sofa and an outdoor porch. Relax in our welcoming accommodations that provide all the essentials of home and more. Choose from a variety of room options, all equipped with full kitchens. Our large one-bedroom 1st floor suites offer beautiful views of the grounds and ocean.

Founders Park is a picturesque park located in Islamorada, Florida, United States. Situated at 87000 Overseas Highway, this park offers a serene escape for visitors to enjoy the natural beauty of the Florida Keys. With lush greenery, scenic walking paths, and recreational facilities, Founders Park is the perfect spot for picnics, family outings, and outdoor activities. Whether you're looking to relax by the water, play sports, or simply take in the stunning views, Founders Park has something for everyone to enjoy. Come visit this hidden gem and experience the tranquility and charm of Islamorada's Founders Park.

Bud N' Mary's Marina is a charming lodging institution located at 79851 Overseas Highway in Islamorada, Florida, United States. Situated right on the water, this marina offers guests the opportunity to stay in comfortable accommodations while enjoying easy access to fishing charters, boat rentals, and water sports activities. With its picturesque surroundings and convenient location, Bud N' Mary's Marina is the perfect destination for those looking to experience the beauty and excitement of the Florida Keys.

Executive Bay Club is a premier institution located at 87200 Overseas Highway in Islamorada, Florida. It offers a luxurious and exclusive experience for its members, featuring top-notch amenities and services. With stunning views of the surrounding area and access to a range of recreational activities, Executive Bay Club is the perfect destination for those seeking a high-end lifestyle in the heart of the Florida Keys. Whether you're looking to relax by the pool, enjoy a game of tennis, or indulge in gourmet dining, this institution has everything you need for a truly unforgettable experience.

Located at 80001 Overseas Highway in Islamorada, Florida, the Amara Cay Resort offers a luxurious and effortless island experience. From the chic coastal style of the rooms and suites to the breathtaking views of the Alligator Reef Lighthouse, every aspect of this resort embodies the essence of the Florida Keys. Guests can enjoy island-inspired cuisine and cocktails with stunning sea views, as well as a variety of amenities and activities such as boating excursions and beach lounging. Whether you're looking for a relaxing beach vacation or an adventurous day on the water, Amara Cay has something for everyone. With special offers for Florida and Georgia residents, military personnel, and other groups, there are plenty of opportunities to save on your stay. The resort also offers a range of activities, from beachside yoga to ocean adventures, as well as delicious dining options at the poolside Tiki Bar and other on-site restaurants.

Located at 81801 Overseas Highway in Islamorada, Florida, Cheeca Lodge & Spa offers a luxurious retreat surrounded by turquoise waters, towering palms, and calm breezes. This oceanfront resort invites guests to experience barefoot luxury and embrace the laid-back lifestyle of the Florida Keys. With a range of thrilling activities, luxurious accommodations, exceptional dining options, and unparalleled relaxation, Cheeca Lodge & Spa promises an unforgettable getaway. Whether you're looking to celebrate love with a picturesque oceanfront wedding or host a productive corporate retreat, Cheeca Lodge & Spa offers the perfect venue. With over 15,000 square feet of meeting space, impeccable service from event planners, and a stunning backdrop of the Atlantic ocean, this resort is ideal for weddings, sales meetings, conferences, and more.

La Jolla Resort is an iconic lodging institution located at 82216 Overseas Highway in Islamorada, Florida, United States. Known for its "Old Florida" charm, the resort offers a front-row seat for stunning sunsets over the Florida Keys. Situated in the heart of the Purple Isle, guests are just moments away from all the island has to offer. Complimentary activities such as kayaking, biking, and fishing are available for the whole family to enjoy. The resort's multi-bedroom bayfront lodges offer modern luxury in a laid-back setting, perfect for families or groups. With Islamorada's unique beauty and wide-ranging attractions, La Jolla Resort is the perfect destination for a memorable Florida Keys getaway.

Lignumvitae Key Botanical State Park is a stunning park and tourist attraction located at 77200 Overseas Highway in Islamorada, Florida, United States. The park features a beautiful tropical hardwood hammock that was once common in the Upper Keys of Florida. In 1919, William J. Matheson, a wealthy Miami chemist, purchased the island and built a caretaker's home with unique amenities such as a windmill for electricity and a cistern for rainwater. Today, visitors can explore his historic hideaway, which now serves as the visitor center for the park.

Ocean Oasis at Ocean Pointe is a luxurious vacation destination located in Tavernier, Florida. This stunning institution offers a range of amenities including a pool, Jacuzzi, tennis and pickleball courts, a private beach, and a marina. Centrally located between Islamorada and Key Largo, guests can easily explore the surrounding areas and enjoy all that the Florida Keys have to offer. Whether you're looking for a relaxing beach getaway or an active vacation filled with water sports and outdoor activities, Ocean Oasis at Ocean Pointe has something for everyone. Contact our real estate and travel agency at 500 Burton Drive to book your dream vacation today.

Happy Cat Snorkel Boat is a travel agency located at 77522 Overseas Highway in Islamorada, Florida. If you're looking for the best snorkeling experience in the Florida Keys, look no further than Robbie's Marina. Come aboard the Blue Heaven with Sundance Watersports for an unforgettable adventure you'll cherish for a lifetime. With two daily snorkel excursions and sunset cruises available, there's something for everyone to enjoy. During your two and a half-hour snorkel trip, you'll have plenty of time to swim with local marine life and explore the diverse underwater ecosystem. Gear rentals are available for your convenience, and the boat is equipped with outdoor showers and a full-sized bathroom/changing room. Whether you're planning a private party, corporate retreat, or wedding party, Happy Cat Snorkel Boat can accommodate your needs.

Overseas Leisure Group, located at 814 Ponce de Leon in Miami, Florida, is a luxury travel agency with a passion for creating unique and authentic experiences in the Americas and beyond. They specialize in providing exclusive rental properties such as Casa Los Cayos in Islamorada, Florida and the Rio Negro Queen luxury floating hotel in Manaus, Brazil. Overseas Leisure Group takes pride in ensuring that each traveler has a personalized and unforgettable experience, working with local insiders to connect visitors to the true spirit of their destination. With a reputation for exceptional service and attention to detail, Overseas Leisure Group is a trusted partner for travelers seeking extraordinary and memorable adventures.

Located at 84001 Overseas Highway in Islamorada, Florida, the Postcard Inn Beach Resort and Marina offers a unique and authentic Keys experience. As the "Sportfishing Capital of the World," guests can bring their own boat or book an excursion to explore the waters surrounding this beautiful resort. With the merging of two Islamorada resorts into one destination, the Postcard Inn Resort & Marina is set to become the heartbeat of the Islamorada Resort Collection in 2024. Offering island-chic guestrooms, exciting culinary experiences, a lively marina, a stunning beachfront, and a variety of activities, guests can seamlessly transition between adventure and relaxation from sunrise to sunset.

Located at 81200 Overseas Highway in Islamorada, Florida, the Kon-Tiki Resort is a charming lodging institution that offers a unique and unforgettable vacation experience. Nestled in the heart of Islamorada, our resort boasts fully-equipped villa accommodations and an unbeatable location on the Florida Bay, making it the perfect destination for those seeking a relaxing getaway. With 23 unit accommodations to choose from, each with its own unique flair, guests can enjoy a range of options including standard rooms, spacious efficiency apartments, and villas complete with a kitchen, living room, and dining area. Our accommodations are designed to provide ultimate comfort and style for our guests.

Islander Bayside Villas is a charming lodging institution situated at 81450 Overseas Highway in the picturesque town of Islamorada, Florida. Nestled along the beautiful bayside, this tranquil retreat offers guests a peaceful and relaxing atmosphere with stunning views of the water. The villas are tastefully decorated and equipped with modern amenities to ensure a comfortable stay for visitors. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Islander Bayside Villas provides the perfect escape in the heart of the Florida Keys.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes. Experience authentic Keys life with island-inspired flavors and legendary cocktails while enjoying stunning sea views. The resort features lush private beaches, pools with ocean views, and fishing charters for the catch of your dreams. Accommodations include suites, cottages, and villas with idyllic Islamorada views and unique resort amenities. Special offers include discounts for Florida and Georgia residents, military personnel, and tax season rewards. Enjoy dining at Wild & Lime and nearby restaurants, as well as unforgettable experiences for special occasions. Plan your dream destination wedding or arrive at the Florida Keys marina for a seamless vacation experience. Explore all that La Siesta Resort & Villas has to offer and make memories to last a lifetime.

Located at 83409 Overseas Highway in Islamorada, Florida, the Chesapeake Beach Resort is a stunning seaside lodging destination that exceeds all expectations. As the Sport Fishing Capital of the World, Islamorada offers a relaxed atmosphere and year-round activities for guests to enjoy. Each room at the resort features comfortable beds and a tranquil ambiance, with the option to choose a Garden View room with a private balcony or upgrade to a suite or villa for added luxury. Surrounded by crystal blue waters and white sandy beaches, the resort offers a picturesque setting for a relaxing and breathtaking vacation.

The Key Lantern Motel is a charming lodging establishment located at 82150 Overseas Highway in Islamorada, Florida. Situated in the heart of the Florida Keys, this motel offers cozy and comfortable accommodations for travelers looking to relax and unwind. With its convenient location near the beach and various local attractions, guests can enjoy a peaceful stay while exploring the beautiful surroundings. The Key Lantern Motel provides a welcoming atmosphere and excellent hospitality, making it a perfect choice for a memorable vacation in the sunshine state.

Seven Sports is a premier sports store located at 80625 Overseas Highway in Islamorada, Florida. With a wide selection of top-quality equipment and gear for various sports such as fishing, diving, paddleboarding, and more, Seven Sports is your one-stop shop for all your outdoor adventure needs. Whether you're a seasoned pro or just starting out, our knowledgeable staff is here to help you find the perfect gear to enhance your experience. Visit us today and gear up for your next sporting adventure!

Breezy Palms Resort is a charming lodging destination located in the beautiful Islamorada, Florida. Situated at 80015 U.S. 1, this tropical oasis offers guests a relaxing and unforgettable experience in the heart of the Florida Keys. With cozy accommodations, stunning ocean views, and a range of amenities including a pool, beach access, and on-site dining options, Breezy Palms Resort is the perfect choice for those looking to unwind and soak up the sun in paradise. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, this resort has everything you need for a memorable stay. Book your stay at Breezy Palms Resort and escape to a slice of paradise in Islamorada.

Evolve Boutique is a trendy clothing store located at 81888 Overseas Highway in Islamorada, Florida. Our boutique offers a unique selection of stylish and fashionable clothing for men and women. From casual everyday wear to chic evening attire, we have something for every fashion-forward individual. Our store is known for its high-quality garments, on-trend designs, and excellent customer service. Visit Evolve Boutique and discover the perfect outfit to help you stand out from the crowd.

Anglers Reef Villas is a luxurious waterfront lodging option located at 110 Anglers Way in Islamorada, Florida. As a combination of a lodging, real estate, and travel agency, Anglers Reef Villas offers guests the opportunity to experience the ultimate vacation in paradise. With stunning views of the ocean, top-notch amenities, and a prime location near popular attractions, Anglers Reef Villas is the perfect choice for those seeking a memorable stay in the Florida Keys. Whether you're looking to relax on the beach, explore the local area, or invest in a vacation home, Anglers Reef Villas has everything you need for a truly unforgettable experience.

The Ron Levy Aquatic Center is a premier aquatic facility located in Islamorada, Florida, United States. Our center offers a variety of programs and services for all ages and skill levels, including swim lessons, water aerobics, lap swimming, and lifeguard training. With state-of-the-art facilities and expert staff, we provide a safe and enjoyable environment for individuals and families to stay active and healthy. Whether you're looking to improve your swimming skills or just relax by the pool, the Ron Levy Aquatic Center has something for everyone. Come visit us and dive into a world of aquatic fun!